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Middletown Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Middletown holiday rentals

A cozy interior with a staircase, leather sofas, a chandelier, and bookshelves filled with books and decorative items.

1. Lincoln’s Loft - Speakeasy Suite

Lincoln’s Loft - Speakeasy Suite
Lincoln
10.0 out of 10, Exceptional, (57 reviews)
"Great place to stay!"
United States
Kyle O.
The price is HK$1,373
HK$2,038 total
includes taxes & fees
15 Oct - 16 Oct
Lincoln’s Loft - Speakeasy Suite
A living room with a brown leather sofa, a city-themed pillow, a kitchen with modern appliances, and a loft-style ceiling.

2. Lincoln’s Loft - Hawthorne Suite Downtown Lincoln, IL

Lincoln’s Loft - Hawthorne Suite Downtown Lincoln, IL
Lincoln
10.0 out of 10, Exceptional, (33 reviews)
"This property is perfect for our family, allowing us all to stay in the same place and relax!"
United States
Sean W.
The price is HK$1,194
HK$1,897 total
includes taxes & fees
13 Oct - 14 Oct
Lincoln’s Loft - Hawthorne Suite Downtown Lincoln, IL
A carpeted staircase with a handrail, a door with a number plate, and a light fixture on the ceiling.

3. "Living on the Wedge" A 3-bedroom house in Lincoln on Historic Route 66.

"Living on the Wedge" A 3-bedroom house in Lincoln on Historic Route 66.
Lincoln
10.0 out of 10, Exceptional, (1 review)
"The place was very clean and spacious. It is decorated Mid Century Modern. 2nd floor is the main floor.We loved the 3rd floor media room where many channels were available to watch/stream. Paddington Bear was watching atop his suit case. There is a half bath on 3rd floor if the need arises while watching shows.The bathrooms were cute. I meant to take pictures. The master bedrooms bathroom had a blue tub and cute pattern wall paper.We slept well.We were in town for our grandson's soccer...
United States
Carol S.
The price is HK$1,962
HK$2,886 total
includes taxes & fees
15 Oct - 16 Oct
"Living on the Wedge" A 3-bedroom house in Lincoln on Historic Route 66.
A modern kitchen with a large island, pendant lights, and a black and white color scheme.

4. Top-Rated Premier Modern Getaway

Top-Rated Premier Modern Getaway
Petersburg
10.0 out of 10, Exceptional, (3 reviews)
"It was super clean, very nicely decorated, and a perfect space for our family of 5. The host is very friendly and communicative."
United States
Hayley P.
The price is HK$1,240
HK$3,904 total
includes taxes & fees
18 Oct - 19 Oct
Top-Rated Premier Modern Getaway
A kitchen with wooden cabinets, a dining area with a table and chairs, and a television in the background.

5. Modern Bungalow Home with Mid-Century Flair

Modern Bungalow Home with Mid-Century Flair
Springfield
8.2 out of 10, Very good, (74 reviews)
"Nice place"
United States
Diane
The price is HK$742
HK$1,651 total
includes taxes & fees
13 Oct - 14 Oct
Modern Bungalow Home with Mid-Century Flair
A two-story Victorian-style house with a wrap-around porch, a prominent tower with a conical roof, and a well-maintained front yard with flowering plants.

6. Elegant Historic Stay | Walk to Capitol & Attractions | Modern Comfort

Elegant Historic Stay | Walk to Capitol & Attractions | Modern Comfort
Springfield
10.0 out of 10, Exceptional, (20 reviews)
"It was a very nicely located and clean property large enough for a family to stay in as they visit the sites in Springfield."
United States
Joseph
The price is HK$1,376
HK$1,567 total
includes taxes & fees
9 Nov - 10 Nov
Elegant Historic Stay | Walk to Capitol & Attractions | Modern Comfort
A large, historic brick building with a prominent tower and arched windows, surrounded by well-maintained lawns and trees.

7. Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm

Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm
Springfield
10.0 out of 10, Exceptional, (65 reviews)
"The Rowland Suite was perfect for our stay in Springfield!"
United States
Robert S.
The price is HK$1,566
HK$1,790 total
includes taxes & fees
14 Oct - 15 Oct
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm
A spa room with a wooden hot tub, a glass partition, and a painting on the wall.

8. Sports complex w/ Hot Tub located near Scheels Sports Park and Lincolns home!

Sports complex w/ Hot Tub located near Scheels Sports Park and Lincolns home!
Springfield
9.2 out of 10, Wonderful, (9 reviews)
"Hosted our second bachelor here and it’s still one of the coolest places we’ve ever stayed! George is an awesome host!"
United States
Tyler B.
The price is HK$7,455
HK$10,396 total
includes taxes & fees
19 Oct - 20 Oct
Sports complex w/ Hot Tub located near Scheels Sports Park and Lincolns home!
A large, historic brick building with a turret and multiple windows, surrounded by a well-maintained lawn and a metal fence.

9. Spacious Carriage House | Private Entrance | Historic & Stylish

Spacious Carriage House | Private Entrance | Historic & Stylish
Springfield
9.8 out of 10, Exceptional, (46 reviews)
"A very spacious lodging that was very clean and very comfortable. Will stay here again when in Springfield."
United States
Christine
The price is HK$1,558
HK$1,783 total
includes taxes & fees
14 Oct - 15 Oct
Spacious Carriage House | Private Entrance | Historic & Stylish
A grand staircase with ornate woodwork and a large mirror.

10. Grand Historic Retreat | Walk to Capitol & Attractions | Timeless Elegance

Grand Historic Retreat | Walk to Capitol & Attractions | Timeless Elegance
Springfield
8.4 out of 10, Very good, (6 reviews)
"Plenty of room for a large group!"
United States
Amy V.
The price is HK$4,367
HK$5,033 total
includes taxes & fees
25 Oct - 26 Oct
Grand Historic Retreat | Walk to Capitol & Attractions | Timeless Elegance
A grand staircase with ornate woodwork and a large mirror.

11. Historic Luxury Stay | Downtown Springfield | Step-Free Access

Historic Luxury Stay | Downtown Springfield | Step-Free Access
Springfield
10.0 out of 10, Exceptional, (17 reviews)
"Great place to stay ! Close to all things Lincoln. "
United States
Patricia J.
The price is HK$1,281
HK$1,464 total
includes taxes & fees
13 Oct - 14 Oct
Historic Luxury Stay | Downtown Springfield | Step-Free Access
A spacious bedroom with a large bed, a television, and a view of the outdoors.

12. Spacious Historic Escape | 4BR Luxury | Walk to Downtown & Landmarks

Spacious Historic Escape | 4BR Luxury | Walk to Downtown & Landmarks
Springfield
10.0 out of 10, Exceptional, (8 reviews)
"We rented the 2nd and 3rd floors and were very pleased with the place. It definitely had the historic charm, was very clean, and very close to all of the historical attractions. Would definitely recommend. "
United States
Chelsea T.
The price is HK$2,645
HK$3,028 total
includes taxes & fees
1 Nov - 2 Nov
Spacious Historic Escape | 4BR Luxury | Walk to Downtown & Landmarks
A large, historic brick building with a prominent tower and arched windows, surrounded by well-maintained lawns and trees.

13. Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury

Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury
Springfield
9.4 out of 10, Exceptional, (31 reviews)
"Beautiful property and a great location!"
United States
Rebecca k.
The price is HK$1,603
HK$1,835 total
includes taxes & fees
13 Oct - 14 Oct
Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury
A large, two-story brick house with a prominent corner turret and multiple windows.

14. Charming Downtown Stay | Victorian Beauty & Modern Comfort

Charming Downtown Stay | Victorian Beauty & Modern Comfort
Springfield
9.6 out of 10, Exceptional, (25 reviews)
"It was very nice. Very friendly host. Location was perfect. "
United States
Dianne H.
The price is HK$1,603
HK$1,835 total
includes taxes & fees
14 Oct - 15 Oct
Charming Downtown Stay | Victorian Beauty & Modern Comfort
A large, two-story brick house with a prominent corner turret and multiple windows.

15. Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location

Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location
Springfield
9.8 out of 10, Exceptional, (8 reviews)
"Great home for large family gatherings."
United States
Eric H.
Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location
Room

16. The coolest most fun house with pool hot tub pool table air hockey and much more

The coolest most fun house with pool hot tub pool table air hockey and much more
Springfield
The price is HK$3,376
HK$3,969 total
includes taxes & fees
13 Oct - 14 Oct
The coolest most fun house with pool hot tub pool table air hockey and much more
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middletown Hotel Reviews

Red Roof Inn Springfield, IL

Red Roof Inn Springfield, IL

8/10 Good
"Clean room"
Edward 2-night trip
Posted 6 hours ago
Red Roof Inn Springfield, IL

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

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Look no further and take a look at our great range of rental properties in Middletown!

Frequently asked questions

Can I find a holiday rental in Middletown?

Yes, there are holiday rentals close to the most popular sights in Middletown, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Middletown has to offer?

Modern Bungalow Home with Mid-Century Flair: This holiday home rental outside of Middletown offers a garden, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in Middletown?

While exploring the area, visit the sights like World's Largest Railsplitter Covered Wagon, Lincoln Speedway and Lincoln's New Salem State Historic Site. In the wider area, you’ll find Illinois State Fairgrounds and Lincoln's Tomb.

What are holiday rentals like in Middletown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middletown. Holiday rentals provide amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a small group gathering.